How Do I Convince Him That I’m Not Like His Ex?

How Do I Convince Him That I’m Not Like His Ex?

I’ve been dating this guy for the past four months. I am 26 and he is 38. We met on Both of us are divorced with no kids. We were both in relationships with someone who treated us like we were worthless. Because of that we both have a hard time trusting that the other isn’t going to be like our ex. I have been divorced for over four years. He, on the other hand, has only been divorced for about nine months. I am his first serious relationship since his divorce. He is not my first serious – I’ve had a couple since my divorce. I am not in this to fall in love and get married right away – I am in this to have a companion. Someone to enjoy spending time with and get to know and see where it might go in a few years.

When our relationship started out, it was great! We enjoyed each other’s company, always laughed, had plenty to talk about. Due to the past couple of relationships I have been in, I took my time to get to know this one. It took me over two months to get comfortable enough with him to feel like he could be someone worth pursuing. But it seemed that as soon as I got on board, he stepped off the boat. He has been distant, doesn’t chat as much, doesn’t come around as much.

We’ve had a couple conversations about it. Each time he says he has hit a brick wall. He’s admitted to being afraid that I am going to turn out like his ex. He wants to go out and do things with his friends and things he enjoys, and he thinks I will be upset about it. I told him as long as he makes time for me too, I am fine with him wanting to have his own life. I told him the other night that if he just doesn’t want to be with me, he needs to tell me and let me go. He said that he wants to be with me, but also wants to be able to do his own thing. So how do I get this guy on board again? How do I prove to him that I am not going to turn out like his ex? And most importantly, how do I trust that he isn’t just dragging me along as just a spare time girl? –Jennifer

I have one overriding dating philosophy: Relationships are easy.

Dear Jennifer,

I have one overriding dating philosophy:

Relationships are easy.

All the people who tell you that relationships are “work” are people who married the wrong people and are justifying their bad decisions.

Sorry to say that, but I believe it to be true. Happy marriages are fun, not work!

That doesn’t mean that every second of the day is heavenly. But it does mean that you should get along with your partner 95% of the time, and the 5% you don’t should be resolved quickly and painlessly.

Sounds to me, 4 months in, that your relationship is a little too much “work” for my taste.

You are the CEO of Jennifer, Inc. and your boyfriend is an intern applying for a job with you.

Case in point: “As soon as I got on board, he stepped off the boat. He has been distant, doesn’t chat as much, doesn’t come around as much.”

Then what’s the point of him, Jennifer?

What’s the point of a boyfriend who is distant, doesn’t call, doesn’t make plans, doesn’t make you feel safe, heard or understood, and generally makes you feel like you’re one more thing he has to deal with?

That’s right. There IS no point.

I’m not sure if you’ve read my materials beyond this blog, but if you had, you would have heard me repeatedly reminding you that you are the CEO of Jennifer, Inc. and your boyfriend is an intern applying for a job with you.

He may have gotten in the door because he’s got a good resume and was a solid interview, but now that he’s been working with you for four months, how is his job performance?

“Each time he says he has hit a brick wall. He’s admitted to being afraid that I am going to turn out like his ex. He wants to go out and do things with his friends and things he enjoys, and he thinks I will be upset about it.”

He may be a good guy, my dear, but he’s a shitty employee.

You need a man who arrives at work early and stays late, all with a big smile on his face.

Unfortunately, you’re acting like the intern, who is just begging for her job: “How do I get this guy on board again? How do I prove to him that I am not going to turn out like his ex?”

You don’t. You’re the CEO. You bloodlessly evaluate his work, not based on his potential, but on his performance. Then you face the facts:

Your intern isn’t cutting it.

It’s time to downsize.

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  1. 61

    It really does seem like it’s nothing more than timing…which means it’s REALLY EASY to fix! 🙂
    Just bring it up earlier in the dating process…heck by date #3 you should be fairly comfortable and talking about values some anyway.
    Again, I think if you take a curious approach (asking about him, his experiences, what he wants) without an agenda,  he’ll be likely to respond positively, and it should stir his own curiosity about you. 

  2. 62

    We talk about it before that point. Not 1st date, but if they get to 3-5 dates it usually comes up naturally. I don’t wait till we are naked and say, tit for tat and please decide in 5 minutes, because I would like to get to this right now if it is a yes. I am confident but not pushy, in what my boundaries are, and never lead anyone on that I wouldn’t want to try a relationship with. I follow Evan’s rules from the book and his advise regarding mirroring and communication. 
    But if it gets close after we have talked about it, I do tell him we have to stop because I want to make sure he is open to it all. I also tell him its hard because this feels so good and right, but I want to feel safe and that we both want this. Good thing is I have never sleep with someone who lied and then didn’t call me the next day (knock on wood), or we didn’t make a solid run at being together after. Downside is it weeds out the 99.99% that aren’t meant for me, and my sex life isn’t nearly is good as it should be. 🙂 No guarantee on a great outcome but it helps when you have taken the time to get to know them and they stick around. 
    For amusement purposes for everyone tonight:  he signed up for 4 other dating sites today: Okcupid, Zoosk, Plenty of Fish, active on Match with new pictures, and Our Time. Yes I checked, and no I didn’t check or craigslist. Gotta wish him the best and pick yourself up! Life of a single girl dating in the city. 

  3. 63

    Julia #60
    The men I’m dating are in the over-40 age range, so you would think they’d have it more figured out by this time. However, I do not rule them out entirely; I still give them a chance, but I’ve found that these men are true to their word, and not looking for anything serious, no matter how excited about me they might seem.

  4. 64

    Agreed with Evan. Love the anology as well! Convincing = problem. Been there, done that, loooong time ago, and it was a slow destroying of my self-respect. The expiration date of that relationship was three month and my pleading and convincing made it last an extra year, where he kept me as a “twice a week girl” for sexual purposes. At least that part was fun. It was of course harder to end it at that point but I did and it was such a relief. Never again did I try to convince a man! I decided that my awesomeness was self-explanatory : )
    I also totally agree with JoeK, Frimmel, and nathan, and I’m actually thrilled to finally read some men’s comments on this issue of “when to bring up the no sex without exclusivity talk”. I remember an old thread where I mentioned my preference for explaining my views on physical intimacy before getting all hard and wet, and there were criticism over that preference. Which is fine, but I’m glad to read about some men’s dislike to be led on to believe that intercourse will happen, only to be told once rock hard that “Nope, for that you need to give me commitment.”
    On the other hand I also relate to nathan’s comment @58: “But I think too much weight gets put on “getting the commitment,” as if that’s the thing that will make everything ok and safe.” It’s of course a necessary baseline (duh!), but it’s really not enough for me. Actually I’ve never even had to deal with non-exclusivity, since exclusivity has always been the dating framework I would operate into. If we want to be wise (which is even better than safe), we need exclusivity + commitment to explore the relationship for long-term potential + already a solid idea that there is enough compatibility of goals, values, communication styles, etc. before going too involved emotionally and physically.
    I stopped having sex, and making out, without having a solid idea of all three. Pursuing a relationship within that framework still does not garantee anything, heck even a marriage does not garantee anything, but it’s much safer than clinging to the elusive promise of exclusivity. And if a man is into you and is open to exploring a potential to something longer-term, he will gladly talk about goals and values, so long as it comes from curiosity and not a demand for a relationship. That’s been my experience and it has worked fine. Now, the tricky part is WHEN and HOW to communicate these preferences. It has to happen pretty quickly, yet AFTER an emotional connexion has been established. To me, the art of dating is to establish such connexion early on AND without the crutch of physical intimacy. When there is an emotional connexion, all these complex conversations become a bit easier, and if this happens relatively quickly, sex is not postponed for too long, and everybody wins.
    And finally, I really like the distinction that Paula makes @49 between “work” and “effort”. I agree with the fact that happy and healthy relationships should not involve the kind of hard work that means struggle, confusion, pain, etc. But to my experience most relationships do require some serious effort, depending on the characters and personalities involved. Being pretty reactive and intense, I can garantee you that it takes ongoing effort on my part to practice self-control and equanimity. It does not make my relationship bad to need that kind of effort. As Karmic Equation wrote in another thread, if it feels good after the fact, it’s all good.

  5. 65

    Ruby #59 “I’ve gotten to the point where I take any hesitation from a man that he isn’t ready seriously, even if he might claim otherwise when asked.”
    It’s interesting. I totally get what you’re talking about here, and the examples you bring up of the places the men are at in their lives. And with men who are clearly either struggling to move on from their past, or who are clearly just looking for fun, you’re approach makes total sense. But it also made me wonder about timing and appearances.
    In my experience, expressing a desire for commitment too quickly isn’t a great sign either. I dated someone last winter (early 2012) who was calling me “soul mate” after a few weeks, and starting to ask me questions about children and the like not long after. For my part, I demonstrated an unwavering desire for a relationship, even after she began to flip about and doubt things. In a lot of ways, the whole experience was like mirroring shadows. We had the right appearances for a short time, but the reality was that it all had moved too fast. As a result, when I met my current girlfriend, who wanted to take things much slower, I was not only ok with that, but actually desired it myself. And this included a delayed demonstration of seriousness and commitment on my part. Not because I wanted something casual, but exactly because of what Fusee speaks of in #65 about developing a more complete picture of someone first. It seems off, somehow, to expect someone to be serious about YOU in a rather short time frame. When they really don’t know you enough to make such a decision.
    Odds are that you’re right the majority of the time that guy X simply isn’t in a place to be serious and commit. However, I have to wonder if sometimes it’s more about not having spent enough time to actually know you. And being able to make that step from a place of confidence, as opposed to from a place of lust, which is where my ex-girlfriend and I both operated from last winter.

  6. 66

    I completely empathize with your experiences, and i think it is probably a mixture of a) coming across men who may *wish* they were available, but who aren’t in reality and b) asking for relationship commitment when it is more appropriate to ask for exclusivity.
    I think the message of “I can’t have sex with you until you are my boyfriend” is very different from “I can’t have sex with you until we mutually agree to not see other people”.  I think the latter is much more realistic and less high pressure, it also puts you in the driver seat because it is something you must BOTH agree to.
    That being said- with my current boyfriend (and former friend for many years), I just said casually with a big grin, “you know if we have sex I’m going to want you to be my boyfriend” and his reply was “I’d be honored.”  So all in all your approach may be a little off, but I think it probably has more to do with not having met the right guy, yet.
    Keep at it, it took me 2 years of fits and starts to finally find myself in a solid relationship BUT I learned so much along the way that prepared me to be successful in my current relationship.

  7. 67

    Contrary to Evan I do believe a relationship can be work until the two of you are in a good emotional maturity stage. But ultimately you want it to be easy. Simply I would not throw the baby and the water until you have explored an issue, communicated well about it and have the inofrmation you need to make a sound decision, and take a step forward whatever it is it will be. We are not all in a great emotional, mature stage in our own mind and skin, relationships, interactions between men and women are not all natural and easy and being mature is also recognising it and working on it. On one side I think it is important you feel good with yourself and maintain your boundaries, know what you want, what you don’t want, how you feel about the situation. If he is telling you he is afraid you will be upset if he has his alone time, it is good information he is sharing with you. Then it is role to react to it an tell him how you feel about it. You can perfectly tell him you feel hurt he is pulling away and tell him exactly how you feel about the issue he raised with you, e.g. you believe it is good you both have your own activities, activities that nurture you, make you happy as an individual. And you value that freedom and me-time. But on the other hand you also value a lot the time and interaction you have together and you want it to be easy and fun and you don’t want to feel like there is an elephant in the room. See how he reacts to you speaking your heart/feelings truly, with calm and confidence, and it can be said warmly and in a very feminine way. His reaction will tell you a lot. It seems to me he is still very affected by his divorce, this is something he has to go through and he must decide for himself if he can leave the past in the past and move to a new relationship and build that trust with someone again. But you can’t make him do anything. You can only tell him how you feel and respond to his actions/reactions. Only from thatplace you can interact well and decide. Good luck!

  8. 68

    Nathan #66
    I’m definitely a proponent of taking things slowly. It’s proved to be a good way to rule out those who want to keep their involvements casual, but it isn’t foolproof. I don’t expect anyone to be serious about me right away, either, just open to a more serious relationship if things go well. My point was that there are always plenty of men who play a hard and fast game of not getting too attached, for whatever reason. They are even fine with dating someone exclusively, as long as it’s just for a few months.

  9. 69

    “We talk about it before that point.”
    Hmmm….ok, I must’ve misunderstood what you meant earlier. Guess I have to agree with Alyssa that these just aren’t the guys for you.
    I love how Alyssa handled it with her boyfriend – light and with humor. Granted they had been friends for some time, so there’s some trust already. I can just imagine his reaction if she had delivered it with more of a challenging tone!
    Liz – all you can do is present your needs in a non-critical, non-adversarial non-challenging way…then it’s on him what to do with that information.

  10. 70

    Hey Liz
    When I knew that I wanted a healthy relationship, I like Evan put into analogy “became the CEO of Gina, Inc… and that meant I had a screening process. There was no way I would end up on a date with a man who did not have time, money, emotional availability and desire for a relationship. I would in a fun and playful way ask their opinions on values and what I wanted that I found most important, and also willing to walk away if they did not meet those factors.  I would listen and ask questions, making sure he didnt just get out of a relationship, sounds like he has a good head on his shoulders and is the type of guy I am looking for. When you qualify someone, you easily disqualify the ones that you may have spent 3-4 dates or more that is not the right man for you.

  11. 71

    Thanks will take this all to heart,
    already feeling a little better.

  12. 73

    Liz 42
    I received some wonderful advice recently: if you steer your life and your heart in the direction you want to go, you will get there.
    One thing I couldn’t help but notice from your post is that you bring up the issue of a committed relationship with guys.  It really should be coming from them.  The only reason we women ask for it is because we feel insecure about the situation. I think it is fine and even a very good idea to express your views about relationships, but be careful how it is done, and is coming from a place of security and self-esteem, and is not asking the guy for something.
    On the other hand, I believe that once you are in a genuinely good place for a relationship, there is not much you can do to scare the right guy away, shy of constant drama and pursuing.

  13. 74

    @ Dina #73:
    Perhaps JB just wants some female company?  Maybe he just wants a little action?  Any number of reasons.

  14. 75

    Normally its after a lot of dates, and on the heels of do we take this to a completely intimate relationship we are both open to, or take a left at the crossroads. No pursuing or drama, they drive the boat, I am just there enjoying the ride for the most part.  
    I think everyone is right, if its right, you are secure, open and happy, (and they are too), and the chemistry is there, no guy would shy away from a discussion, albeit at the right time and tone, about what both parties are looking for. Oh, and its not they don’t call me back after it comes to a head, or meet me. That is when the whole “I have been thinking about us” and the lets be friends talk happens. Stars will align soon enough. Timing is everything. 🙂 Good to know a lot of us are out there fighting the same fight.

  15. 76

    Excellent reply Evan! All of my life I have been told that a good relationship requires work to sustain. As a result, I found myself in relationships where I was trying to prove myself and win the object of my affections over. Oftentimes, I stayed in a no win situation longer than I should. 
    Older and wiser now, I have gotten pretty darn good at screening and weeding out men who are not going to make good partners for me. 
    Better to be happily single than miserably married.

  16. 77

    @Fusee #65
    “And if a man is into you and is open to exploring a potential to something longer-term, he will gladly talk about goals and values, so long as it comes from curiosity and not a demand for a relationship.
    Wow – so well put, Fusee!
    Asking questions with an agenda is often obvious, and makes men skittish. It tends to come across like the agenda (having a realtionship/marriage) is more important than discovering if the woman truly likes the guy/if they share values.

  17. 78

    @ Fusee # 65
    I second Joe K… well put!!!  (As usual, I might add.) 🙂

  18. 79
    Karmic Equation


    May I ask how long you were married and if your husband was your first lover?

    I’m only asking this because it seems you put so much weight on “being in a relationship” before intimacy, it sounds very virginal.

    While you may have been married, you seem virginal-minded and are acting/communicating very much like a virgin. Not a judgment, just an observation. I think this post ( might shed some light on why the men you’ve been dating have acted the way they have.

    I’m not sure you can change your mindset, which is kind of sweet. You might have better luck if you dated secularly? Like trying ? I would think that people on secular sites date in a way that is more aligned with the way YOU naturally think about sex.

    Just a thought.

    Good luck.

  19. 80

    No a virgin at all and its not a religious requirement. It
    has just been how I have always been. I did have an interesting
    conversation with a man I use to date last year. I don’t normally
    remain friends with those people that I have dated, but he is a
    wonderful man. He was dating me and another women at the same time.
    After 3 months we talked about where this all was going and how I
    wanted to feel safe to continue to see him and move forward as he
    desired.   He admitted that because of the divorce (3 years
    and hundreds of thousands of dollars in attorneys’ fees) he wasn’t
    open to falling in love again or giving all of himself. He just
    held back a lot and I am a very passionate, bubbly, touchy feely
    person. I told him I understood and with a few tears stopped seeing
    him. But he continued to see the one women, still is. He said we
    have been sleeping together for so long, but I still have
    commitment issues. I said how can you sleep with someone for a
    year, and not love and want to be committed to that one? His
    response: the good catholic girl (I am not a practicing catholic he
    was teasing me) wouldn’t wait to see, and this one took what I was
    willing to give. At first I was jealous, I wanted to be in her
    place, as I truly connected with this man and did love him. His
    daughter adores me and has emailed me and said you were my fathers
    match and soul mate (she is 18). But then I thought about our
    discussion on timing, he still isn’t ready so in the end it is all
    about timing. If I had sleep with him, I would be in her position
    begging for him to open up, trying to fix a broken man, and not
    fulfilled at all (and we know that is not a good place). Even
    though I said I was taking a break I did go out with someone last
    night that was a great deal of fun. I needed to get out.
    Admittedly, I thought about the CFO all last night and the 5
    internet site guy, which I felt guilty about. 🙂

  20. 81

    @Dina Strange#73 Joe is right. We’re men and (at 52 yrs old) we have to take what we can get if you want a little company, a little sex etc….. I’m not going to be celibate and lonely just because I can’t find someone I have deep feelings for. Life goes on. I don’t offer monogamy or a time limit if I can’t deliver it. It’s that simple.

  21. 82

    @Liz 42
    Liz, I feel for you because I´ve been in your shoes. I used to be very open, sincere, but it didn´t work with men. My advice is this: When you feel the man has started withdrawing, don´t panic and force yourself to let him distance himself. Don´t ask him anything relationship related, just casual things. Because when you ask directly and the guy isn´t ready yet, it doesn´t necessarily mean that he will never be ready. Maybe he just needs more time to work out his feelings towards you. So when you ask him, he doesn´t know what to respond so as not to hurt you he decides to tell you “let´s be friends.” If you let him go, however, he will always be back, believe me. And when he returns, he will know how he really feels, so you´ll get your answer without uselessly spoiling your chances by being impatient. And that´s why I agree with Evan that dating casually more than one man is a good idea because you don´t focus all your expectations on one person.

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